Hilton, Lohan & Niarchos

Hilton and Niarchos announce their breakup. A week earlier, with Hilton in Austria, Niarchos spends several nights partying with Lindsay Lohan. Upon Hilton's return to L.A., she heads to nightspot Shag with Arizona Cardinals and former USC quarterback Matt Leinart, where they are spotted by Niarchos. After a 3:30 a.m. screaming match, the pair officially calls it quits. A month later, a video is released of Hilton laughing and egging on childhood friend Brandon Davis as he goes on a 10-minute insult-filled diatribe about Lohan, whom she later has a wordless dance-off with in a New York hotspot.

August 22

Tears Either Way

"I like, cry, when I listen to it, it's so good," Hilton tells Blender of her debut album, Paris. Critics cry too, for a different reason. USA Today gives it 1½ stars, declaring that "Hilton's colorless, wafer-thin singing reminds us there are still limits to what technology can do for the human voice."

September 07

Double Burger, Hold the Cuffs

After pulling out of In-N-Out Burger, Hilton is arrested in Hollywood on allegations of driving under the influence. Police observed Hilton driving erratically and she measured .08 on a Breathalyzer test, the minimum to warrant an arrest. "I had one margarita, starving 'cause I had not ate all day," Hilton tells Ryan Seacrest the next day. Charged with two misdemeanors, Hilton accepts a plea agreement that includes 36 months probation.

October 08

Hilton & Richie Reunite

Hilton and Richie, who are set to film season five of The Simple Life in the fall, have a friendly dinner at West Hollywood restaurant Dan Tana's. The feuding friends appear to have put their differences aside, laughing through the meal and leaving the eatery smiling, hand in hand.

2007

January 23

'Paris Exposed'

The website Parisexposed.com, displaying Hilton's personal documents, diary entries and home videos, launches. The site claims the materials were obtained after Hilton failed to pay rent on her storage facility and the items were auctioned off. Hilton files a lawsuit against the Web site and a judge shuts it down.

Paris Hearts Benji

Hilton steps out on the arm of Good Charlotte band member Benji Madden – twin brother of Nicole Richie's boyfriend Joel. On her MySpace Celebrity blog, Hilton writes, "I've never felt so happy and in love. He's such an amazing guy and life has never been better." But, while searching for a companion on MTV's reality show, ParisHilton'sMyNewBFF, Hilton and Madden call it quits after nine months together.

2009

Paris Digs Doug Reinhardt

"He makes me feel like I've never felt before," Hilton tells PEOPLE of "sexy boy" Doug Reinhardt. "Everything he does is romantic. He's amazing and we're really happy. He's beautiful, he's smart, he's well-educated and he treats me like a princess. We're just very much alike." The pair, who date on and off for a year, call it quits in June 2010.